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Tanya Van Court’s great idea, the one that would become not only her next business venture but her all-consuming passion, began simply enough. Her daughter, the older of her two children, was turning nine. When Van Court asked her what she would like for her birthday, her daughter replied that she wanted only two things: a bicycle and money to open an investment account. Van Court thought these were laudable goals, but she knew it wasn’t going to happen. She knew – we all know – that well-meaning relatives and party guests were likely to brings a few arts-and-craft kits, maybe a board game, and several versions of the fad-of-the-moment (rubber band bracelet, anyone?)

“Sometimes we walk down a path because it’s easy and comfortable. We may never meander, and consequently miss the new opportunity right in front of us. Change doesn’t have to be bad; change can be wonderful.”

Van Court saw a problem – a broken gift-giving system – and thought she could come up with a way to fix it. She had always taught her children the concept of Share/Save/Spend as a way to handle the money they earned. It occurred to her that she could set up an online system that would allow gift-givers – friends, grandparents, aunts, uncles, anyone – to contribute directly toward these goals. More personal that simply writing a check, the gift giver would view a child’s profile and see their specific saving, spending and donating goals, and then decide how much and to what fund they’d like to contribute. “My daughter very much appreciates the gifts people give her,” Van Court says, “but it doesn’t necessarily mean she actually uses them. I wanted to fix what I see as a broken economic exchange, and just as importantly, teach our kids the value of all this money that’s being spent.”

It happened that right around the time of her daughter’s birthday, Van Court had been trying to decide on her next career move. She received both her undergrad and master’s degree in industrial engineering from Stanford University in the early 90’s and after trying out various engineering jobs she began working her way up the corporate ladder, first at CableVision, then at ESPN and later Nickelodeon, which suited her well because of her passion for children and education. From Nickelodeon she moved on to her most recent position at Discovery Education, where she helped launch the first digital textbooks. But Discovery Education had just gone through a major restructuring and Van Court found herself out of a job and trying to figure out her next career move.

Van Court had been planning to look for another corporate position, but the more she thought about her online gift giving idea the more she started to think that maybe she didn’t want to continue on the corporate ladder, after all. “I’m not one of these perennial entrepreneurs who’s always seeing opportunity wherever I look. I wasn’t looking for a business venture.”

Still, she wanted to explore the possibilities. She read a book called The Lean Start-Up, by Eric Ries, and followed the book’s recommendation to talk to as many people as possible. And when Van Court did that, she was floored by the positive feedback she got. “People said, ’Do this. Not today, not tomorrow, but yesterday.’ I have friends from every socio-economic background, and it didn’t matter if the person was a working-class mom, or a person with millions of dollars in the bank. They all felt that their kids had too much stuff, and that kids weren’t learning lessons about healthy financial habits. They thought that this could fix the problems that they were experiencing with gift giving – both in terms of their own kids and as far as buying presents for other kids.”

So in early 2015 Van Court made the decision not to return to the corporate world but instead to turn her idea into a reality. Naming her company Sow, she put together a website using all the feedback she had received. Her company was officially launched on December 3, 2015, one day before her son’s 6th birthday. Naturally, he has his own Sow account. Van Courts says, “An amazing proof of concept came when my son got $250 for his birthday towards meaningful goals, instead of receiving meaningless goods.” The site has already signed up hundreds of young people and parents during its first month.

Van Court’s daughter, Gabrielle

Financially, there have been and continue to be many sacrifices involved in not collecting a regular paycheck, but her family and friends have been extremely supportive, including her ex-husband (she refers to him as her Wasband) with whom she maintains a great relationship. Still, she cautions others to be careful. “You have to be realistic about your prospects. It’s likely you’re not going to go a couple of months without income, you could go a year or more.” Still, the financial sacrifices, which have not been insignificant, haven’t deterred her. “Sometimes we walk down a path because it’s easy and comfortable. We may never meander, and consequently miss the new opportunity right in front of us. Change doesn’t have to be bad; change can be wonderful.”

One big change for Van Court was learning to ask for help. “When you are working as an executive you have a lot of leverage and power to help other people, and you don’t need to ask for as much. When you are an entrepreneur that whole paradigm gets completely shifted upside down. You ask for help with everything.” One neighbor helped her get together a focus group of kids in the neighborhood. She reached out to another friend who had expertise in branding, another with marketing experience. A friend who is a graphic designer helped her develop a logo. “I literally reached out to almost every person I could think of in my network to help with something. I was so grateful, and continue to be so grateful, that people were so willing to help. I was almost in awe. I’d never asked for so much help in my life; it’s just not in my nature. It was a real growth and learning experience for me.”

Despite the hard work and financial sacrifices, Van Court, 43, has no regrets and remains passionate and upbeat about her mission. “I have not wavered from the belief that this is the right product and I am the right person to bring it to market. I believe that this has the potential to be a great business and have real social impact. It’s the opportunity to leave the world a little better. Where I sit today, there is nothing that I would rather be doing and nothing I could be more excited about.”

Van Court’s startup tips:

Be realistic about your prospects and about how long you will go without a paycheck (hint: probably longer than you think). Be clear on what sacrifices you will need to make.

Read the book, The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses by Eric Ries. Then talk to people and get as much feedback as you can.

Ask for help. You might be amazed at people’s willingness to help, but you have to ask.

Don’t minimize the power of networks, and know that you’ll need to grow and expand yours to succeed.

If you have the grit, the toughness, to endure the sacrifice, doing something you believe in is wonderful.

DeAnne Wingate hasn’t had a paycheck since 2010. Instead, she’s been living off the savings she put away from her days in internet advertising. It’s difficult and she knows the money won’t last forever, or even much longer, but at this moment she believes she is doing exactly what she was put on this earth to do.

Her career began in the late nineties, when much about the internet, and internet advertising in particular, was still new. Her early career was exciting, and it’s not without some fondness that Wingate looks back. “It was like the New Frontier; we were setting the rules as we went along. It was a great challenge, and great fun.” She worked first in Boston, then Chicago, and finally in New York City. “Having a corporate position in New York City was kind of the apex, the ultimate dream,” she says.

But at the same time, something didn’t feel quite right. “I knew that there was a bigger purpose for my life. I knew there was something beyond doing what I was doing. I felt heart palpitations every time I got on a plane, and I think my heart was telling me that this was not the path I was supposed to be on. This was not the way that I was supposed to be living my life.” (more…)

Leslie Fishlock is an unrepentant geek and self-declared rabble-rouser who loves nothing more than to disrupt.

Questioning her tactics for getting more women into tech, a smug woman once criticized her for “teaching old ladies how to open PDFs.” She was far off base in terms of what Fishlock and her organization Geek Girl is actually doing, but the 50-year-old founder admits if that’s what it takes to help them understand technology, then she’s all for it.

“She totally missed the concept that if you don’t start somewhere learning how to do things for yourself, you’re never going to get into more advanced fields like aerospace or engineering. Maybe I’m not training astronauts of the future but I certainly am making technology accessible.” (more…)

What’s your lie? I asked this question to a recent client of mine who was feeling very stuck with what she wanted to do regarding a major life decision. She couldn’t answer me on the spot, she needed time to think. But I have a lie…let me tell you about it.

For 11 years, I worked to build a non-profit organization in service of helping immigrant and refugee women start their own businesses. They faced systemic challenges in getting their businesses up and running – mostly due to language and economic barriers. In 2010, I took a sabbatical from my organization to recover from burnout and to figure out what was next for me. I was relatively free of stress during my sabbatical; it gave me the opportunity to really experience life in a way I had never been able to in my adult career and to realign my passions with my work.

What became clear to me was my commitment and support of women’s empowerment. I also valued freedom and independence greatly. (Yes, I was the type of kid who would look at our shed outside my suburban NJ home and wish I could live in it by myself.) I wanted to empower and work with women, regardless of whether or not they were immigrants. When I came back from sabbatical, I realized my lie was deep inside, I was not the one who should be running this organization. I knew it should be led by the people it sought to serve – by fellow immigrant women in the community. Only they really knew and understood their circumstances and challenges and could organize and represent themselves in a way where they shared power and were the ones making change.

We had developed an innovative curriculum in the process, and I believed that could be spearheaded independently of the organization by a motivated entrepreneur who could take it to the next level. At first, I thought that entrepreneur was me but, on further reflection, the thought of raising capital and driving forward another start-up – which would take everything I had – made me cringe.

This realization only came to me after stepping away from what I was doing and giving myself a break. I actually had no idea about the amount of financial stress I had been under all those years running the organization. Don’t get me wrong; we did AWESOME work. The team was even more AWESOME, and our clients – amazing.

When I started working with low-income women entrepreneurs and was thinking of starting the organization, an early donor – herself an immigrant – suggested to focus on immigrant women. She hadn’t seen anything substantial being done for the community in this respect. In some way, it had felt as if I had been partially carrying someone else’s agenda all these years and not been feeling my full authenticity. There were elements I felt I owned, but in the spirit of a non-profit, at the end of the day, I worked on behalf of the interests of donors and institutional funders. I never felt stuck, per se, but the year upon returning from my sabbatical, I knew it was time for a change. I acknowledged my “lie” and what the right decision for the organization was.

Being clear with myself on what I really wanted to do was key. It took time and space to figure this out but, when I finally did, everything seemed to flow like a river. No more getting sick. No more stress. No more feeling like I was pushing a boulder up a hill. I could just flow, knowing I was on a path to live my truth: to work one-on-one with successful women and leaders, in service of their personal and professional transformations, and guide them in using their success to have a positive social impact on individuals and the planet. While all these years I had dedicated myself to working on behalf of women with few resources, I knew my calling was to work with women who had the resources to give back.

Sometimes we do good work, and it is not exactly the path that we know will most fulfill us. Sometimes we do work that sucks the life out of us. It’s what Greg Levoy, author of Callings calls a “parallel path”. It’s like the dancer who becomes the dance critic or the novelist who instead ends up in journalism. Don’t get me wrong; sometimes parallel paths are very necessary. But what is your “truth” that keeps popping up? What are you hiding from? What parallel paths do you keep creating for yourself to avoid your real path? Give yourself space and time to reflect. If you don’t, you will feel stuck, unmotivated, and even sad.

I was fortunate to have the time and space to figure this out. I was able to explore and make so many different discoveries about my next steps. If you cannot make physical space or take time off, it’s critical to make mental space. Keeping a journal and adding a self-reflective process to your regime will help immensely with this.

So what’s your “lie”? Really mull it over. See what comes to you. You may be surprised at what pops up and how this bit of information can help ignite momentum for your next big leap, whether it’s a career change or new business idea. The other way to explore this (also great advice from Greg Levoy) is to have someone ask you over and over: “What do you KNOW to be true?” Have them keep asking it and see what it uncovers in you.

Farhana Huq is an award-winning social entrepreneur, executive coach, and founder of several globally conscious ventures including Brown Girl Surf. You can find out more about her at www.surflifecoaching.com.

Conventional is not a word that could be used to describe Ronni Kahn. The self-described spiritual sexagenarian and founder of Australia’s leading food rescue charity, OzHarvest, possess a motley accent that’s difficult to pin down and an enthusiasm for her work that’s bursting at the seams. She claims to be genetically blessed with a huge energy field and lucky to have parents who were extraordinary role models. But – blessed or not – Kahn herself is an inspiration to anyone seeking greater significance in life.

After many years of self-discovery, she finally understands how good it feels to have passion and how passion can motivate action. “I didn’t start OzHarvest because I was a bored housewife, I wanted purpose and meaning. I am so fortunate to do what I do.” (more…)

Rare is the medical research professional who would give up an established 23-year career to start a healthcare clinic in Africa. Fewer still are those who would fund it out of their own pocket, eating through their savings and foregoing retirement benefits. Meet Margaret Kilibwa, clinical nutritionist and social entrepreneur.

“I wasn’t prepared when I made the leap, but I suppose if I knew then exactly what it would take, I might not have jumped into it. Then again, when I’m at the clinic, many women come to tell me ‘you saved my life’ but even if it was one woman it would be enough for the amount of investment I’ve made.”

Kilibwa was born in Sabatia not far from Kisumu, on the banks of Lake Victoria in Western Kenya. Influenced by her American classmates at boarding school, the young graduate crossed the Atlantic to study chemistry at the University of Cincinnati, where she had won a scholarship. From Ohio, she was accepted to the prestigious Cornell University where she did a Masters, followed by a PhD in clinical nutrition. Although she was interested in going to medical school, Kilibwa decided to gain work experience instead, “not in the diet area but rather to understand in more practical terms how nutrition can be used to prevent disease,” she recalls. (more…)

Not everyone is as lucky as Joi Gordon. She discovered early in her career that she needed to make a change, that job satisfaction and happiness could only result from doing something that propelled her out of bed in the morning. And while Joi may have been lucky in her timing, she says it’s never too late to do what you love, especially if what you love is living a life of community service in the non-profit sphere.

“The best time to explore the possibilities is when you can volunteer. Find out what you’re passionate about, and give your time and your talent. Join boards and get oriented with the operations of an organization. Understand what is required to run a non-profit organization. When the time is right, make the switch. Because there will be a right time. There’s always a right time for a person to refocus, reshift.”

An only child, Gordon grew up in Brooklyn before moving to Oklahoma where she studied radio and TV broadcasting at the University of Oklahoma. Those were the heydays of court TV and Gordon was sure she wanted to be a court reporter, covering scintillating trials and breaking down legalese for the average Joe. Heeding the advice of a professor who recommended she get an institutional understanding of her preferred beat, Gordon opted for a juris doctorate from her Alma Mater.

As a means to an end of a career in legal journalism, Gordon returned to NY to take a position with the Bronx District Attorney’s Office. All was going to plan until the newly minted public prosecutor switched on the local news one morning before work.

Gordon recalls vividly, “It was the usual busy morning, trying to get out the door for work when I was distracted by a story on a not-for-profit that had just opened its doors six months earlier. The organization, Dress for Success, was appealing for donations of women’s business attire to help them in their work of getting disadvantaged women into the workforce.

She left that day for work, planning to contact the organization only about dropping off some items. Speaking with the young founder, Nancy Lublin, Gordon was inspired. The 22-year-old had dropped out of law school to launch Dress for Success with a $5000 inheritance from her grandfather. Teaming up with some nuns from Spanish Harlem and supplementing her income by playing poker in Atlantic City, Lublin was shameless in her pursuit of resources for her non-profit. As soon as she heard Gordon was a lawyer, the entrepreneurial Lublin offered her an unpaid position on the Board of Dress for Success.

Gordon immediately felt a connection with the organization and appreciated Lublin’s passion. She signed on with the Board and provided oversight as Dress for Success began to build out the platform to expand its operations beyond New York. After a little over one year, and only 29-years-old at that time, Gordon knew she had found her passion and signed on full-time to run the Dress for Success New York office as Lublin took on a worldwide role: “I left what I was doing without even questioning it. I cannot say I grew up wanting to be in the helping profession, but I decided this was going to be my path, my journey, and my opportunity to make a difference. My decision was met with mixed reviews from my parents. My mom was always a strong supporter of me, if I was happy, she was happy. My dad, an immigrant from the West Indies, was less sure. Being a lawyer meant having status, he was definitely more concerned about the shift and didn’t understand how his only child, a lawyer, decided not to do that anymore. But he came round and before his death last year told me how proud and happy he was that I made that decision all those years ago.”

Gordon ran the NY Office for three years until Lublin decided to step down from the organization to write the next chapter in her life, inviting Gordon to step into the CEO role in 2002. In addition to suiting up women for job interviews, under Gordon’s leadership, Dress for Success has focused more intently on employment retention and offers resumé-writing support, interview training, and general all-around confidence building. “It’s not unusual for us to work with women who have spent 20 years in the corporate world, lost their job, and then lost their way. They need an organization like ours to pick them up again. We work with non-profit job training agencies offering hard skills training like computer training or a culinary program, for example. They refer a woman 48-72 hours before her interview, and we help get her ready. If she doesn’t land the job, we help her further along the process to help her find employment.”

Dress for Success has helped more than 775,000 women find work and is now in 136 cities in 17 countries around the world. “I never would have imagined to have operations in so many countries and find this common denominator, not only in the women we serve, but the women who serve the women we serve – our volunteers. They are so passionate about helping women overcome obstacles and succeed,” Gordon says proudly.

Gordon acknowledges it was easy for her to make the transition. She was young, with a husband and child, but no debt as she had gone to law school on a scholarship. She was also earning a modest salary as a public prosecutor so her day-to-day expenses were reasonable. But based on her experience with Dress for Success, the 46-year old CEO is adamant in her belief that women must discover their own inner motivations. “If you don’t move forward, you’re standing still. Join a board, do your research, get involved in organizations that you believe in and feel strongly about. Figure out the timing. Look for the right opportunity but it must be strategic, you’ve got to do your homework and you need to get involved. There are so many opportunities for people to get involved in the non-profit sector first as a volunteer, then as a Board member and hopefully then as an employee.”

Being in so many cities worldwide, Dress for Success offers many volunteer opportunities for women looking to get into a new field, learn new skills, or even get a foot in the door. They can serve as image consultants in the boutiques, helping clients getting suited for interviews. Others can work in the career centers, reviewing resumes and doing mock interviews. “Women of a certain age have such wonderful experience in the workforce to offer. We get great use out of retirees to act as speakers for our numerous workshops for example.”

And the best thing about volunteering is that you become a known quantity to a whole group of people previously outside your network. So while you may not have a lot of experience in that new field, your passion and commitment will be proof of your reliability, putting you in serious contention for a job in the organization should one arise, or in similar organizations where others can vouch for you. Volunteering also does wonders for one’s confidence and feeling of fullfilment.

As Joi says, “I’m incredibly fortunate to have a job that combines my commitment to public service with my passion for women’s issues. Volunteering is wonderful in that it offers that opportunity to everyone.”

If you are interested in becoming a volunteer with Dress for Success, information is available here.

Encore is an organization targeting men and women in midlife careers looking not only for continued income but the promise of more meaning – and the chance to do work that means something beyond yourself. Read an earlier Career 2.0 profile on Jere King who did an Encore fellowship.

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Srirupa Dasgupta admits she rarely listens to other people. Well, to be fair, she listens to what other people say and then makes her own decisions. The Bengali Indian is a doer, that much is clear. But her story is not what you expect. The force behind this tenacious woman who has sported many career hats is a desire to live her values and invest in her beliefs. For Dasgupta, working with and developing people is her life’s goal, and she is prepared to sacrifice more than most of us to make this a reality.

Born in Calcutta, India, Dasgupta first came to the United States to study at Smith College, with only an aunt to her name far away in California. She double-majored in computer science and studio art, two seemingly unrelated fields. “Being Indian, I was told I need to do something practical and majoring arts was not going to cut it so I did computer science, which was up and coming. But really it made sense, I was drawn to the problem solving and elegant algorithms.”

Fresh out of college she became a programmer analyst for a decision-support software provider for the healthcare industry. After four years and looking for something more interesting, she moved from application and systems development to a management role. For the next 15 years, Dasgupta held various management positions in the software industry, rotating from managing R&D teams and call centers, to developing strategic partnerships and consulting services for different blue-chip companies in Massachusetts and California.

In the lead up to the tech bubble burst, Dasgupta started thinking about changing careers. “I had worked the entire lifecycle of the software product, done the whole rotation. I wanted to do something new and fresh.” With much foresight, she launched into a 1-year Integral Coach® training and certification program while still working at Lucent Technologies. “In all of my management positions, what I loved best was working with people, setting a vision and creating opportunities for them to excel and advance in their career … coaching seemed like a good fit.”

In a-not-unwelcome turn-of-events, Dasgupta was laid off from her job in 2002. Well prepared when she got the news, she put all her energies into finishing the coaching certification program. “The training was really aligned with my interests. The methodology takes an integrated approach to the multi-dimensional individual, we looked at the whole person, cognitive, and physical, and the cultural, social and environmental context in which they find themselves. All of these are critical components of coaching, the end goal of which is not to solve the problem, but rather develop the person.”

She started her own coaching practice shortly thereafter. “Even though I had a lot of experience in business, being a small business owner was really different … the first year was a lot of learning-by-doing. I found it difficult to promote myself, attending events and generating leads was challenging.” But not one to shy away from a challenge and noticing she was not alone in her discomfort for business networking, she started a blog to coach herself and others, which led to a book on the subject entitled Effortless Networking.

In fact these evolving career transitions have become a theme and pattern in Dasgupta’s life. As she explains: “Most of us set a goal and move towards it. It’s a linear task. But training as a coach introduced me to another option … it’s called improvisation. You have a map, you know how you will get there, but on route life throws you curveballs. I try to keep my goal in focus but adapt along the way. Coaching has taught me to look at the opportunities that arise and use them to propel me towards my objective rather than seeing them as a distraction.”

After the birth of her second child in 2006, she decided to put her practice on hold as the family relocated to Ohio and finally Pennsylvania for work. For about two years, Dasgupta didn’t actively seek out clients. When she began to think about working again, she found herself at a crossroads. “Should I restart my business? Do something different? Take a salaried position?” she wondered. While thinking about all the possible options, a digital communications and marketing position opened up at nearby Franklin & Marshall College. Although she has been working there for six years and it’s interesting work, Dasgupta admits, her passion lies in working with people.

And so comes the next transition or, more precisely, expression of who she is. Attending an event where Muhammad Yunus, founder of Grameen Bank, was speaking, Dasgupta was intrigued by the idea that one can create a for-profit business with the intention of solving a social problem. As an entrepreneur, her interest was piqued and she started to look around for inspiration while doing her day job at F&M.

Dasgupta learned about the refugee population in Lancaster City and felt a connection. Her own family had been refugees from Bangladesh and she had grown up with stories about how difficult it was to start over in India. At the height of the economic crisis, it was tough for refugees to find work. For the women, it was close to impossible. Thinking about how she could create jobs for these Bhutanese, Iraqi and other female refugees, Dasgupta hit upon the idea of starting a catering business. “These women may not be able to speak English but they can cook!” she realized.

She found a commercial kitchen that rented space on an hourly basis and worked with about four women, who – for practical, mostly language, reasons – cooked what they knew. The enterprising Dasgupta launched the ethnic catering business as a proof-of-concept to see whether she could use a for-profit business model to hire women who otherwise could not find a job, whether the women could do the work, and whether she could pay a living wage.

“All of this was hypothetical. On paper, everything looked great but usually the problems you anticipate are not the ones that show up,” she recalls. “During the first year, I learned all kinds of things and hurdles emerged where I never expected them.”

Apart from the language barrier, a key issue was that the refugees are on welfare. When they get a job, their benefits are cut. But as the catering business is erratic … one day they may get a gig, the next day not. So the irregularity of income wreaked havoc with the calculation of women’s welfare benefits. “Sometimes they had cash, sometimes they didn’t. It was almost easier not to work!” Dasgupta stopped hiring new employees and tried to stabilize the hours of those she already worked with but the problem persisted.

And so, making a decision that no one in their right mind facing a similar challenge would make, this past March, after three years of solely catering, she opened a restaurant. Entirely self-funded and managed all while still working a full-time job in F&M, this remarkable woman is determined to make a go of it. Upohar (which translates to gift in Bengali) opened its doors for lunch and takeout only and offers catering services. Dasgupta’s right-hand man, Stephen, does the deliveries, inventory, and shopping and her staff of five cook and run the show. Dasgupta breaks even but pays for the advertising and marketing campaigns out of her own pocket. She has yet to give herself a paycheck. She is hoping each month she will generate enough revenue to pay her staff and the rent for the following month. So far, so good!

Why all the risk and stress? “I was called to do it. It was the only way I could generate steady employment for these women. Upohar was conceived as a gift for employees, who get the opportunity to work, a gift to the community to try all these new different foods, and a gift to myself. Through working with these women who are starting over, working hard to rebuild their lives from scratch, I have been given the gift of perspective. My problems don’t seem that big anymore.”

And so Dasgupta takes it one day at a time. She now hires not just refugees but also disadvantaged women from shelters. She is hopeful that Upohar will become a place where people come not only come to enjoy the food but also to appreciate all that they have by meeting those who make the food and who have overcome great challenges.

If you are ever in Lancaster City, Pennsylvania, explore the world through food and visit Upohar.

Ask for help. No one does anything alone. Acknowledge your strengths and find help in areas that are not part of your skillset.

Pay attention to your gut reactions and your behavior (what you actually do, versus what you think you do or want to do) – to different situations, events, and people – and use this information in your decision-making process.

Know your limits so you can set and maintain your boundaries. This can help you focus on what matters most and avoid over-extending yourself.

Discussion

Have you ever considered putting your career where your heart is by creating a social enterprise?

Jane DiGiacomo’s life story could easily be a film. The credits roll as she crosses the western prairies in her 31-foot Airstream camper, new husband and young child in tow, seeking out the important things in life and leaving law and a lot of baggage behind. But DiGiacomo is not an actress. She’s the real deal: a confident, happy woman who fearlessly gave up what most people spent their whole lives working towards, financial success and prestige, to experience the smaller pleasures in life: “I’m not special, we all are remarkable, we just have to see it in ourselves.”

Jane, Miles and the mega-cool Airstream

Always attracted to understanding life’s fundamental problems, DiGiacomo studied philosophy at Barnard and was aiming for a PhD. But she fell into law when her father thought this a ridiculous plan. “He said he would only pay for me to go to ‘professional’ school so I guess this planted the seed that I probably should find a career where I could support myself.”

Paying her own way in the end, she attended the University of Minnesota, transferring in her third year to Columbia Law. From there, DiGiacomo worked as a litigation associate for three years in Manhattan. But city life was not really her thing, so she moved to East Hampton, Long Island, where she joined a regional law firm. “I did more independent, directly rewarding work and started building my own client base.”

After two years, DiGiacomo had risen up the ranks and was on serious partnership track. And then came what she calls “The Big Pause”.

In the midst of a divorce, DiGiacomo found herself at a crossroads. She started meditating regularly with zen sangha – studying with Peter Matthiessen – something that became a very important part of her life.

Her zen practice led her to take a leave of absence to sort out her feelings. The move shocked her partner champions at the firm: “I made no promises, I told them I was going away to do a meditation retreat for at least three months, maybe more, and that maybe I wouldn’t come back … It was kind of a big deal,” she adds with a chuckle.

She easily rented her small East Hampton house over the summer and headed north to join the monks and nuns at Gampo Abbey, a Buddhist Monastery in Nova Scotia for four months. “I got a really good picture of what that life would be like should I go in that direction. But it didn’t matter what I did. My neurosis followed me. I was still going to have to deal with my need to be valued and achieve external confirmation. I knew I had to go back to life and face it, I couldn’t run away anymore.”

Picking up where she left off, DiGiacomo rejoined the firm “continuing in high-powered mode.” And then, when she was 33, she got pregnant from a short-term relationship just around the same time she made partner at the firm. In addition to work, she dove into school and community activities to build up her life in East Hampton.

But keeping busy at work and in the community was not enough. “Even though I was doing well financially, the fact that it was just a means to an end was becoming really evident to me … I considered starting my own firm but this wasn’t something I was ready to take on as single mom. So I started working out of our smaller office where I had the chance to focus on local clients and test the idea of going out on my own. It was going well, and then I met Miles.”

Her life turned upside down as she travelled out West to see her new steady. She fell in love, not only with him, but also the expansiveness of the western landscape. “I knew it was going to be difficult to stay where I was.” Soon after Jane met the love of her life, her mother developed terminal cancer, a life event that opened DiGiacomo’s eyes to the truth – life is too short, don’t compromise. “When she died I knew I was done.”

She took some time off to extract herself from her life: “Mom’s death readjusted my perspective. Having Miles in my life freed me to consider other options as he’s a computer programmer and able to work anywhere.” The plan was set. At 39-years old, she quit her job, they sold their respective homes and bought an oh-so-cool Airstream to traverse the country looking for a home. “We pretty much took off. We literally did not know where we were going.” The idea was to spend time in a few towns where they thought they might like to live.

Ultimately, Nelson, British Colombia fit the bill perfectly.

“It was no small thing because we had to immigrate. I couldn’t work for the first four years and instead stayed home with Kell and our two new children, Ziji and Elka.” Once their immigration status was resolved, DiGiacomo looked into becoming a small town law practitioner but was overwhelmed by the commitment involved: several exams, followed by a badly paid 6-month apprenticeship, commuting every day, and leaving kids in day care. “Then I realized I didn’t have to do that. Being successful financially was not what I needed. It was liberating that I didn’t care anymore.”

Once she had accepted this fact, the next steps were easy. She decided to earn a living doing something she really enjoyed and cared about deeply. And so she started looking more closely at community services and not-for-profit work. She is currently the Executive Director of the Nelson and District Hospice Society, a community organization provides volunteer hospice services. In that capacity, she also works closely with Kalein Hospice Society, which has an expansive mission including encouraging dialog about how we create care for the dying and how this influences how we live our own lives. DiGiacomo is drawn to the work because it centers around questions with which she has struggled her whole life “Why are we here? What are we doing with our lives day-to-day?”

For DiGiacomo part of the answer has been coming face-to-face with one’s own death. She does not mean this in a morbid way but rather living the reality of knowing how precious our lives are. Her advice? Don’t get lost in the dream of achieving something. Get out there and do it. That’s what will make it all worthwhile.

Jane DiGiacomo’s Tips for Success:

If you are a working mom feeling torn about where you are spending your time, but also feeling like you are not cut out to be a stay-at-home mom, just do it (if you can). Spend some time with your kids. It will change who you are. It may encourage you to make different decisions about your career and future.

Once you no longer prioritize money, power and prestige, it’s a relief. You realize what’s important and it’s not that stuff. It’s really not about THE STUFF.

Discussion

Are your possessions, salary and prestige holding you back from finding true happiness?

When Lisa McLish was enrolling in law school at Catholic University more than two decades ago, she vividly remembers pausing briefly to consider the joint law/social work degree on offer. Something about the idea of social work spoke to her, but the extra year — of school and debt — turned her off, and she quickly dismissed the thought. After all, she knew wanted to be a public interest lawyer, and for that, she mainly needed a law degree.

“Looking back, I could have easily gotten a joint degree, but I didn’t take the extra time.”

After law school, McLish realized the type of public interest law she had dreamed of doing was harder to practice than she thought. “No one tells you before law school that those jobs are actually very hard to get.”

So initially McLish took a clerkship and then moved over to the Justice Department where she spent nearly 15 years doing government contract work. McLish was happy, in a way, at Justice. “I was a trial lawyer, and I liked that part. It was actually kind of exciting.” There were also supplementary perks. “Being a lawyer gives you an automatic cache; it’s nice but also hard to give up. Everyone kind of understands what you do even if they don’t really understand.” (more…)